Hi Jim,
I've been on that journey recently and I did what drives and reading I could, before I drove myself mad, and here is what I found, and are my opinions:
996 - scare stories around IMS bearings. It does affect the cars (realistically only a very small percentage, but the Internet makes it sound like every other car), but if you buy a car that has the IMS bearing done/has a thorough inspection, there should be no reason to worry.
I wanted a 4S and think they Ss are the best looking 996s and I feel the 996.2 are slightly nicer looking cars than .1s on the whole. You will get people talking about the lights and shared Boxster parts, but it's not all about looks, it's about how it drives for you.
Prices of 996 should be more affordable (I dont know your budget) than 997s, but, think about if there is a fault/issue what you may have to pay out, you might not want to spend the whole budget on the car. The interior may look dated compared to a 997, but, the car at its youngest is 14 years old. Look at any vehicle at that age and tell me it's modern.
997 - Avoid Gen 1 'S' models, was advice I took away from two independents, the issues they found with Gen 1 'S' models was as bad for bore score and issues as the 996 IMS issue.
997 'look' more modern to a 996, but, as above, it's about the drive. I found the 997 steering wheel too thin and too easy to drive. Now, don't get me wrong, I don't want to fight with a car to drive it, but I also want to feel involved. The 997 for me, wasn't as involving as the 996.
In every case, if you care about looks, and a 'newer' car, go 997. If you want a purer 911 drive, go 996 2S (depending on your ability, I felt more comfortable with 4WD). The 997 Gen Ss will set you back more, and for that money, there are some great 996 Turbos available out there. But, go with what is the better drive and feel for you and, for peace of mind, buy from a Indy/dealer, with a warranty.
Hope that helps.
Mark